Abstract
The title compound, C36H58O8, was prepared from 20(S)-protopanaxatriol, which was degraded from Panax quinquefolium saponin with sodium in glycerine, extracted and seperated by flash chromatography. Three six-membered rings are in chair conformations, the five-membered ring is in an envelope form and the tetrahydrofuran ring has a conformation intermediate between half-chair and envelope. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, and C—H⋯O contacts also occur. The absolute structure was assigned on the basis of the synthesis.
Highlights
The title compound, C36H58O8, was prepared from 20(S)protopanaxatriol, which was degraded from Panax quinquefolium saponin with sodium in glycerine, extracted and seperated by flash chromatography
Three six-membered rings are in chair conformations, the five-membered ring is in an envelope form and the tetrahydrofuran ring has a conformation intermediate between half-chair and envelope
Molecules are linked by O—HÁ Á ÁO hydrogen bonds, and C—HÁ Á ÁO contacts occur
Summary
Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.005 A; R factor = 0.045; wR factor = 0.115; data-to-parameter ratio = 9.1. The title compound, C36H58O8, was prepared from 20(S)protopanaxatriol, which was degraded from Panax quinquefolium saponin with sodium in glycerine, extracted and seperated by flash chromatography. Molecules are linked by O—HÁ Á ÁO hydrogen bonds, and C—HÁ Á ÁO contacts occur. The absolute structure was assigned on the basis of the synthesis. Related literature For background to the medicinal uses of Araliaceae-type natural products, see: Shibata et al (1985); Takano et al (1999); Yu et al (2007); Wang et al (2010). See: Iljin et al (1982); Shi et al (1992)
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